By the end of the first week, Jack was sure he was going to go mad. He had never gone this long without masturbating and it seemed his locked up little penis tried to erect every few minutes. He was constantly sitting in a tub of hot water. His penis was so sore from fighting with the unforgiving cage, Jack feared it would be permanently damaged. Forget about looking at online porn. Jack had to avert his eyes every time an attractive woman happened by. “What have I gotten myself into,“he wondered? More than once, he had entertained attempting to pick the lock and forgetting the whole thing, but he couldn’t bear having to face being a failure to Lady M. She had invested so much in him and said he belonged to her. When he would send his required daily chastity pic, she would always text back how proud she was of him and how much it turned her on to keep him locked. He just couldn’t bear the thought of disappointing her.Thinking of Lady M gave him the strength to go on. As the days wore on, things got a little better, and the “moments of desperation” became less and less frequent. His first two weeks in chastity were almost up and Lady M had mentioned giving him some relief if he had been good. He looked so forward to seeing his Keyholder again.

On Friday, Jack received a text from Lady M. It read:LM: Jack, be at our normal meeting place on Sat, 10am. How has your week been going? I think about you often!Jack: I am doing better and better each day. Thinking of you helps me get through the difficult times. Thank you for being my Keyholder!LM: I love being your Keyholder! Knowing that I have a virgin boy permanently locked in chastity really makes me hot! You are a naughty boy, Jack, for turning me on so much. You be good for me tomorrow and don’t disappoint even when faced with the unexpected.Jack: I’ve been a good boy and I won’t disappoint you. I am looking forward to the relief you mentioned.LM: I bet you are. Don’t be late!!

Jack didn’t give much thought to Lady M’s statement about facing the unexpected, he was thinking only of seeing her and getting some relief from his decidedly horny condition. His Saturday would turn out to be more unexpected than he could have ever imagined.When he returned home, there was a package on the front porch. He thought it might have been delivered to the wrong address but his name and address was clearly on it. Jack opened the box and found two full gallons of Fleets enemas. A note was inside and it read, “Prior to our Saturday appointment, use these enemas per the instructions on the container until you run clear water”. It was signed; Lady M. Jack was really puzzled now. Why would Lady M want me to take an enema? He wondered. He thought about texting her, but decided to just do what she asked. He did not want to risk her getting upset at him and lose her promised relief. He finally concluded that this must have been what she meant by expecting the unexpected.

Saturday arrived and Jack was, again, sitting in his car outside the suite. He was about to get out and go in when his phone beeped with a text from Lady M.

LM: Hi Jack. Just wanted to advise you that something came up that needs my immediate attention and I won’t be there today. Ms Pat will be there to take care of you. Please obey her as you would me and remember your protocols. She will report to me afterwards, so don’t disappoint me. I’m so bummed out that I can’t be with you today but I’ll be thinking of you. Be a good boy!

Jack was beside himself. How would Lady M give him some relief if she wasn’t there? Amid his deep thought and confusion, he was about to text back when he noticed it was 5 minutes after ten. He was late! He opened the door and ran for the suite in a panic. As he jerked open the suite door, standing there in a black leather skirt and white blouse with her arms crossed and a stern look on her face was Ms Pat. She looked directly at Jack and said. “You are late!! Get undressed and get in here NOW!!” Jack undressed as quickly as he could and hurriedly stumbled into the back room. “I’m so sorry, Ms Pat, Lady M texted me and……….” She cut him off mid-sentence. “I don’t want to hear your excuses!” Ms Pat said. “Let me inspect your device”. Jack instinctively clasped his hands behind his back. While she did her inspection, Jack noticed a strange contraption in the room that wasn’t here on his last visit. It looked sort of like a saw horse, but has small padded benches and straps in various places. He had no clue as to its purpose.

“Looks as if you wearing into your new chastity device just fine, Jack. I see no signs of bruising or abrasion. What has your wearing experience been like so far?” She asked. “It was very difficult at first, but it’s getting better with time”, said Jack. He was somewhat embarrassed telling Ms Pat, but he decided to go ahead. “Ms Pat, I have never been so frustrated and horny in all my life. Sometimes I can hardly stand it. I was looking so forward to the relief that Lady M had promised me” Jack continued, looking at the floor to avoid her gaze. “Oh, I bet you were, Jack!” Ms Pat said. What did you think she was going to do? Unlock your device and jump your pretty little bones?” Jack continued to look at the floor. His face was so red. “Oh, how cute, you are blushing” Ms Pat said. “Well, today is your lucky day, Jack! I am going to give you some release from your frustration after we have a talk about other matters. Come over here and let’s get you ready.” Now it was Jack that was shocked. Did Ms Pat want to have sex with him?

She walked over to the sawhorse like contraption and pointed at it. “Come over and let’s get you strapped in and I’ll explain what we are going to do”, she said. Jack was still confused, but he walked over and she helped him get positioned on the milking bench. As she got started fastening all the straps she said, “What we are going to do, Jack, is called a milking”. She held up a dildo in her hand. “We will work this rubber cock into your ass and stimulate your prostate gland and all that nasty cum will just drain right out. It will feel like you have to pee but just let it go, don’t try to hold it back. After you get used to it, you’ll find it quite pleasurable, I’m told.” Ms Pat turned and walked over to the desk. Strapped down as he was, Jack couldn’t move enough to see what she picked up but he was plenty concerned. When she walked back over, Jack could see she had something with straps on it and her rattan cane. “Now Jack, as to the matter of your lateness”. Jack was panicky. “Ms Pat, I’m so sorry, please don’t”, Jack said. Ms Pat continued, “Do you remember what the discipline part of the chastity contract said, Jack?” Jack shook his head from side to side. “Well, let me remind you. It said that any failure to comply with our instructions will result in punishment. When infractions happen, they are dealt with immediately.” She put her fingers under Jack’s chin and pulled his head upwards so they were eye to eye. “Jack, I am going to cane you for your failures today. I’ve been caning young boys for many years so, although it will be painful, I won’t injure you. Afterwards, you are forgiven for your failures and it need not be mentioned to LadyM. Won’t that be better than disappointing your Keyholder and hurting her feelings? Wouldn’t you do anything to avoid that?” Jack nodded his head. “Very good, now open your mouth, Jack” He complied and felt a large rubber knob enter his mouth until a flat rubber piece sealed it. Ms Pat fastened the straps behind his head. “Jack, you can cry out as much as you need to. This will help mute the sound so our neighboring suites won’t be nosy. I am going to give you five strokes with cane, Jack. Just accept them and go with it. Remember you are doing this for Lady M. Let’s get this over with and we can move on to giving you some much needed relief” Jack nodded but he was genuinely scared. Ms Pat got into position and, with little fanfare, set about delivering the strokes. Jack tried his best not to cry out, but after the second stroke, he simply couldn’t hold back and cried out. All that came out from the gag was a muffled sound. After the last stroke, Jack’s ass was on fire and tears were streaming down his face.

Ms Pat walked around and gently held his head in her hands. “All is forgiven, Jack, the slate is clean”, said Ms Pat. “Now it’s time for some pleasure”. She walked back to his rear and he felt a spray on his ass and much of the pain lessened. “This analgesic spray will ease the pain for a bit so you can enjoy your milking” she said. Then he felt cold lubricant on his anus and Ms Pat slid one finger in, then two. Sliding in as far as they could go, she liberally spread the lubricant around. She then positioned the machine that would slowly saw the dildo in and out of Jack’s ass for as long as Ms Pat wanted. She quickly rolled a condom on the dildo, lubed it up, and started the milking. With the gag still in place, all Jack could do is moan. It did not go unnoticed by Ms Pat that, although Jack’s small cage would permit very little erecting, his little penis was bulging out of the cage all over and starting to drip clear pre-cum after only a few minutes. Jack’s moaning was getting louder and louder. Finally, cum simply oozed out of the cage until he was completely drained. Ms Pat left him strapped and gagged while she removed the fucking machine and cleaned Jack’s behind up. She, then removed all the straps and the gag. Jack didn’t move.

“Jack, come over to the couch with me”, said Ms Pat. She helped him off the milking bench and led him over to the couch. She sat down and instructed Jack to kneel before her and lay his head in her lap. Then she leaned down and whispered in his ear, “I know what you are feeling, Jack. You are more aroused than ever before and it’s going to be a while for these feelings to subside. I’m proud of the way you took your caning. You know, it can have a cleansing effect, much like a confession of sorts. You have no more burdens. I have many young and older boys who love my caning, Jack. One of them even ejaculates while being caned. Do you think you could ever come to love my caning? Who knows what might happen. You might come to crave being caned.” Jack did not reply. He only put his arms around Ms Pat’s waist and tightly held her. She gently ran her hand through Jack's hair. Right at this moment, he would do anything she wanted. “You are a good boy, Jack,” She said. Jack was still highly aroused, but he wasn’t the only one. Pat closed her eyes and smiled. Even after 20 years of caning young men, it still made her panties wet. Damn you, Lady M, she thought. I am going to send you a laundry bill for cleaning panties. Then she looked down at Jack, smiled again and thought. Maybe I'll just have Jack handwash them at his next milking.